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Volumn 72, Issue 13, 2007, Pages 4635-4643

Tuning of the prolyl trans/cis-amide rotamer population by use of C-glucosylproline hybrids

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL ANALYSIS; ROTAMERS; SUBSTITUENTS;

EID: 34250835794     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0700833     Document Type: Article
Times cited : (17)

References (57)
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    • For recent reviews on the use of glycosyl amino acids as peptidomimetics. see (c) Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491-514.
    • (2002) Chem. Rev , vol.102 , pp. 491-514
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  • 14
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    • Two examples have been reported: (a) Zhang, K.; Schweizer, F. Synlett 2005, 20, 3111-3115.
    • Two examples have been reported: (a) Zhang, K.; Schweizer, F. Synlett 2005, 20, 3111-3115.
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    • Hanessian, S.; Mcnaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854 and references 3a-h and 4a-k in ref 17.
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    • It has been reported that substitution of D-proline by cis-3-hydroxy-D-proline (HypC3-OH) in the sequence Boc-Leu-Pro-Gly-NHMe resulted in a novel pseudo-β-turn-like nine-membered ring structure involving an intramolecular hydrogen bond between LeuNH: Chakraborty, T. K, Srinivasu, P, Vengal Rao, R, Kiran Kumar, S, Kunwar, A. C. J. Org. Chem. 2004, 69, 7399-7402
    • It has been reported that substitution of D-proline by cis-3-hydroxy-D-proline (HypC3-OH) in the sequence Boc-Leu-Pro-Gly-NHMe resulted in a novel pseudo-β-turn-like nine-membered ring structure involving an intramolecular hydrogen bond between LeuNH: Chakraborty, T. K.; Srinivasu, P.; Vengal Rao, R.; Kiran Kumar, S.; Kunwar, A. C. J. Org. Chem. 2004, 69, 7399-7402.
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    • NMR analysis of the crude reaction mixture containing 5 did not indicate the formation of the other diastereoisomer.
    • NMR analysis of the crude reaction mixture containing 5 did not indicate the formation of the other diastereoisomer.
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    • GOESY is a 1D selective NOESY experiment. It provides quantitative information and much higher sensitivity compared to NOESY. First appeared in Stonehouse, J.; Adell, P.; Keeler, J.; Shaka, A. J. J. Am. Chem. Soc. 1994, 116, 6037-6038.
    • GOESY is a 1D selective NOESY experiment. It provides quantitative information and much higher sensitivity compared to NOESY. First appeared in Stonehouse, J.; Adell, P.; Keeler, J.; Shaka, A. J. J. Am. Chem. Soc. 1994, 116, 6037-6038.
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    • A 40-ms Gaussian pulse with a 560-ms mixing time was used.
    • A 40-ms Gaussian pulse with a 560-ms mixing time was used.


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